Brig. Gen. H. Judson Kilpatrick led the disastrous Union cavalry raid on Richmond in late February 1864.

Brig. Gen. H. Judson Kilpatrick led the disastrous Union cavalry raid on Richmond in late February 1864. (Courtesy of the National Archives)

Mark St. John Erickson

History may look upon Brig. Gen. H. Judson Kilpatrick's Feb. 28-March 3, 1864 cavalry raid on Richmond as an embarrassment if not a fiasco.

But you might not have known that from what one observer described as "the rollicking, devil-may-care appearance of the retiring raiders" as the dusty, mud-covered column of nearly 3,000 troopers rode into the safety of the Union lines at Williamsburg on the evening of March 3.

Though the daring expedition from the Army of the Potomac's cavalry headquarters in Culpeper County had failed in its attempt to liberate Federal prisoners, it had "freed" a considerable array of civilian apparel on the way, writes Williamsburg Civil War historian Carol Kettenburg Dubbs in her book, "Defend this Old Town: Williamsburg During the Civil War."

And as Union Provost Marshal David Cronin recalled in his memoirs, the blue-clad horsemen had decorated themselves and their mounts with "spoils taken not for their value, but in the spirit of wanton mischief.

"One had adorned his horse with net armor made out of a hoop skirt; another wore a lady's 'skoop-bonnet' with a huge bow. A large number wore stove pipe beaver hats of antique model, piling them up upon one another."

Williamsburg "had never witnessed anything quite so gay and flaunting," Cronin added, "or so wholly ignored by the inhabitants, as the long column of Kilpatrick's raiders, riding by fours and retaining their regalia."

Known as "Kill Cavalry" Kilpatrick for the wanton casualties his command had sustained during the Battle of Gettysburg and other actions, the flamboyant West Point graduate of 1861 was no stranger to the Peninsula.

As a captain in the celebrated 5th New York Volunteer Infantry -- also known as Duryee's Zouaves -- he fought at Big Bethel on June 10, 1861 in the first battle of the war, during which he became the first regular Union army officer to sustain a wound in battle.

After his recovery, he raised and became the commander of the 2nd New York Cavalry, the unit with which he first won fame as an unusually aggressive if sometimes mistake-prone horseman.

Among Kilpatrick's most spectacular feats was a raid near Richmond conducted as part of the May 1863 Chancellorsville Campaign, during which Maj. Gen. George Stoneman's cavalry was ordered to penetrate deeply behind the Army of Northern Virginia's right flank and threaten Gen. Robert E. Lee's railroad and supply lines.

Though the expedition failed to cut Lee off, Kilpatrick drew considerable attention in the press by riding around Lee, then capturing wagons and burning bridges almost to the outskirts of Richmond. Eventually, he withdrew to the southeast, where he "found safety and rest" within the Union lines at Gloucester Point after a total march of 200 miles.

Not long afterward, Kilpatrick and the 2nd joined Union infantry from Yorktown and the Navy gunboat USS Commodore Morris for a May 19-20, 1863 raid into Mathews, during which they took 300 horses and mules, 150 head of cattle and 150 sheep while burning five mills and substantial stores of grain and flour intended to supply the Confederacy.

Promoted to brigadier general after his return, Kilpatrick may have been relying on the familiarity he gained during his May 1863 dash around Richmond to plan a raid designed to liberate Union prisoners at Belle Isle and Libbey Prison nine months later.

"If you succeed in liberating the prisoners you will conduct them within our lines at Williamsburg," wrote Army of the Potomac Chief of Staff Maj. Gen. A. A. Humphreys, issuing orders for the daring expedition.

Despite reports that the Confederate capital was defended by only 3,000 men, however, not everyone was swayed by Kilpatrick's confidence, including cavalry corps chief Maj. Gen. Alfred Pleasanton, who bet Kilpatrick $5,000 that he would not achieve his objective.

Those reservations soon proved worse than true despite the fact that Kilpatrick and his force of about 3,500 troopers came as close as 1 mile to the capital.

Disorganized from the outset, the column met unexpectedly stiff resistance after it failed to stop a Confederate train that spread the alarm to Richmond.

Harried by sleet, snow and rain, it also was surprised by a deadly Confederate cavalry pursuit led by Maj. Gen. Wade Hampton.

"The enemy charged," Kilpatrick later wrote in his report of the clash with Hampton's men, "and considerable confusion ensued."

Soon afterward, Kilpatrick and his horesmen retreated down the Williamsburg road through New Kent County, leaving behind a second, smaller force of 500 cavalrymen with whom they had planned to rendezvous in Richmond.

Splintered in two -- then ambushed after fleeing to King and Queen -- this column of about 200 troopers led by Col. Ulric Dahlgren was mostly lost except for the survivors who escaped to Gloucester Point -- and Dahlgren's stripped body was displayed in Richmond after the discovery of papers describing the killing of Confederate President Jefferson Davis as part of the raiders' mission.

To the west, Kilpatrick and his much larger detachment succeeded in making their way to New Kent Court House, where a force of 1,000 cavalry, 2,000 infantry and an artillery battery under the command of Col. Robert M. West from Fort Magruder waited to shield their March 3 retreat to Williamsburg.

"I have reached Gen. Butler's line with my command in good order," Kilpatrick reported in a telegram sent to his commanders through Fort Monroe.

Still, Kilpatrick had lost some 350 men killed or wounded during the raid and a startling 1,000 taken prisoner.

And despite leading a punitive raid into King & Queen to avenge Dahlgren's death shortly afterward, his reputation was badly tarnished.

It was a "ridiculous and unsoldierly raid," Confederate cavalry command Maj. Gen. Fitzhugh Lee wrote bluntly in his report.